JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
Which one of the following is the strongest base in aqueous solution?
- ATrimethylamine
- BAniline
- CDimethylamine
- DMethylamine
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Correct answer: C
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Concept used: In aqueous solution, the basic strength of amines depends on:
- the effect of alkyl groups, which increases electron density on nitrogen and makes it more basic,
- solvation of the protonated amine in water, which stabilizes the conjugate acid.
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Compare the given amines:
- Aniline (): The lone pair on nitrogen is delocalized into the benzene ring by resonance, so it is much less available for protonation. Hence, aniline is the weakest base here.
- Methylamine (): A primary aliphatic amine. The methyl group gives a effect, increasing basicity compared to ammonia.
- Dimethylamine (): A secondary amine. Two methyl groups increase electron density on nitrogen, and in aqueous solution its conjugate acid is still reasonably well solvated. This makes it very basic.
- Trimethylamine (): Though it has three methyl groups giving strong effect, in aqueous solution the protonated form is less effectively solvated due to steric hindrance. So it is less basic than dimethylamine in water.
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Order of basic strength in aqueous solution:
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Therefore, the strongest base in aqueous solution is:
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Option check:
- A: Trimethylamine — Incorrect
- B: Aniline — Incorrect
- C: Dimethylamine — Correct
- D: Methylamine — Incorrect
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